Rapamicina - Moligand™, ≥95%(HPLC) , CAS No.53123-88-9

CAS: 53123-88-9 Cat. No.: S293790 Fórmula: C₅₁H₇₉NO₁₃ Peso molecular: 914.19 Número CE: 610-965-5

GRADE & PURITY Moligand™, ≥95%(HPLC)

Synonyms

AY 22989 | AY-22989 | CHEBI:9168 | EC 610-965-5 | HMS2089A21 | RAPA | (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl

Storage

Armazenar a -20°C, carregado com árgon

Shipped In

Arca de gelo + almofadas de gelo

Visão geral

Anti-fúngico e imunossupressor. Inibe seletivamente o alvo da rapamicina nos mamíferos (mTOR) e bloqueia a ativação subsequente da quinase p70 S6 (IC50 = 50 pM). Inibe especificamente o mTORC1, mas o mTORC2 que fosforila a Akt a Ser473 parece ser insensível à rapamicina. Impede a ativação translacional do IGF-II. Também impede que as células T em repouso entrem no ciclo celular, mas não interrompe diretamente a progressão do ciclo celular. Demonstrou inibir eventos de sinalização posteriores, como a fosforilação de p110Rb, a ativação da quinase p34cdc2 e a síntese da ciclina A. Apresenta uma forte ligação às proteínas de ligação do FK-506. Também foi referido que induz apoptose numa linha de células B murinas, inibe a proliferação celular induzida por linfocinas na fase G1 e detém irreversivelmente as células de Saccharomyces cerevisiae na fase G1.

Specifications

Sinónimos

AY 22989 | AY-22989 | CHEBI:9168 | EC 610-965-5 | HMS2089A21 | RAPA | (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl

Especificações e pureza

Moligand™, ≥95%(HPLC)

Mecanismos bioquímicos e fisiológicos

Um antibiótico trieno macrocíclico que se liga e inibe o alvo molecular da rapamicina (mTOR). Forma um complexo com FKBP12 que se liga e inibe o alvo molecular da rapamicina (mTOR). A rapamicina é um potente imunossupressor e tem ação antica

Condições de armazenamento de armazenamento

Armazenar a -20°C, carregado com árgon

Enviado em

Arca de gelo + almofadas de gelo

Grau

Moligand™

Pureza

≥95%(HPLC)

Nomes e identificadores

Pubchem Sid

504763502

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504763502

Sorrisos canónicos

CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC

IUPAC Name

(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

InChIKey

QFJCIRLUMZQUOT-HPLJOQBZSA-N

INCHI

1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1

SMILES isoméricas

C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)O)C)/C)O)OC)C)C)/C)OC

RTECS

VE6250000

Peso molecular

914.19

Reaxy-Rn

5848501

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Macrolide lactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Macrolide lactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolide lactams
• Alternative Parents: Alpha amino acid esters Macrolides and analogues Cyclohexanols Piperidines Oxanes Tertiary carboxylic acid amides Carboxylic acid esters Cyclic alcohols and derivatives Cyclic ketones Hemiacetals Lactams Lactones Azacyclic compounds Dialkyl ethers Oxacyclic compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Organopnictogen compounds Organonitrogen compounds Organic oxides
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Macrolide lactam - Alpha-amino acid ester - Macrolide - Alpha-amino acid or derivatives - Cyclohexanol - Oxane - Piperidine - Cyclic alcohol - Tertiary carboxylic acid amide - Cyclic ketone - Secondary alcohol - Carboxamide group - Carboxylic acid ester - Hemiacetal - Ketone - Lactam - Lactone - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Oxacycle - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Organopnictogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aliphatic heteropolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
• External Descriptors: Plyenes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Alvos associados (humanos)

FKBP1A Tclin Peptidyl-prolyl cis-trans isomerase FKBP1A (10 Activities)

Discover Target: FKBP1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP1B Tchem Peptidyl-prolyl cis-trans isomerase FKBP1B (1 Activities)

Discover Target: FKBP1B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP5 Tchem Peptidyl-prolyl cis-trans isomerase FKBP5 (1 Activities)

Discover Target: FKBP5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EIF4E Tchem Eukaryotic translation initiation factor 4E (1 Activities)

Discover Target: EIF4E

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDCD4 Tchem Programmed cell death protein 4 (1 Activities)

Discover Target: PDCD4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MTOR Tclin Serine/threonine-protein kinase mTOR (7 Activities)

Discover Target: MTOR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Propriedades químicas e físicas

• Solubilidade: Soluble in DMSO at 50mg/ml or methanol at 25mg/mlSoluble in alcohol, dimethyl sulfoxide and dimethyl formamide. Insoluble in water.
• Sensibilidade: Heat sensitive.
• Rotação específica [α]: -150° (C=0.2,MeOH)
• Ponto de fusão (°C): 177 °C(dec.)
• Peso molecular: 914.200 g/mol
• XLogP3: 6.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 913.555 Da
• Monoisotopic Mass: 913.555 Da
• Topological Polar Surface Area: 195.000 Ų
• Heavy Atom Count: 65
• Formal Charge: 0
• Complexity: 1760.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 15
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 1